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York Suede Chelsea Boot

York Suede Chelsea Boot

Men's Blake McKay York Suede Chelsea Boot - Brown - Casual boots A supple suede finish brings modern sophistication to a sleek Chelsea boot grounded by a cushioned footbed and a durable rubber sole. more

$165.00 $109.90

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York Chelsea Boot

York Chelsea Boot

Men's Blake McKay York Chelsea Boot - Black - Casual boots Tough yet tasteful, the York Chelsea boot from Blake McKay has everything to earn a spot in your collection. This slip-on boot with a soft suede upper, dual elastic gores and OrthoLite... more

$109.99

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Best Seller
Shawn Chelsea Boot

Shawn Chelsea Boot

Men's To Boot New York Shawn Chelsea Boot - Brown - Casual boots Classic Chelsea style defines this handsome suede ankle boot furnished with an arch-supporting cushioned footbed for superior comfort. Pull-on style with elastic gore insets Cushioned... more

$450.00

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Muller Boot

Muller Boot

Men's To Boot New York Muller Boot - Brown - Casual boots Tonal stitching and a burnished upper add modern sophistication to an Italian-made boot grounded by a durable lug sole. Side zip closure Leather upper and lining/leather and rubber sole Made in... more

$498.00 $348.60

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Shelby Ii Chelsea Boot

Shelby Ii Chelsea Boot

Men's To Boot New York Shelby Ii Chelsea Boot - Brown - Casual boots A flexible combination sole adds rugged grounding to this Italian-made Chelsea boot crafted from sleek calfskin leather with a cushy, arch-supporting footbed. Cushioned footbed with... more

$399.00

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Burkett Cap Toe Boot

Burkett Cap Toe Boot

Men's To Boot New York Burkett Cap Toe Boot - Brown - Casual boots Polished calfskin leather adds sophisticated shine to a classic Italian boot with a smart arch-support insole and flexible rubber sole. Lace-up style Removable, cushioned insole with... more

$495.00 $331.65

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Burkett Cap Toe Boot

Burkett Cap Toe Boot

Men's To Boot New York Burkett Cap Toe Boot - Brown - Casual boots Polished calfskin leather adds sophisticated shine to a classic Italian boot with a smart arch-support insole and flexible rubber sole. Lace-up style Removable, cushioned insole with... more

$495.00

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Largo Chelsea Boot

Largo Chelsea Boot

Men's To Boot New York Largo Chelsea Boot - Brown - Casual boots Supple calfskin elevates a handsome Italian Chelsea boot with an arch-support footbed for all-day comfort. Pull-on style with elastic gore insets Leather upper and lining/rubber sole Made... more

$475.00

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Largo Chelsea Boot

Largo Chelsea Boot

Men's To Boot New York Largo Chelsea Boot - Brown - Casual boots Supple calfskin elevates a handsome Italian Chelsea boot with an arch-support footbed for all-day comfort. Pull-on style with elastic gore insets Leather upper and lining/rubber sole Made... more

$475.00

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Bedell Chelsea Boot

Bedell Chelsea Boot

Men's To Boot New York Bedell Chelsea Boot - Brown - Casual boots A handmade sole with hammered brass nails grounds a rustic Italian boot with a smart arch-support footbed. Pull-on style with elastic gore insets Leather upper, lining and sole Made in... more

$595.00

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Largo Chelsea Boot

Largo Chelsea Boot

Men's To Boot New York Largo Chelsea Boot - Black - Casual boots Supple calfskin elevates a handsome Italian Chelsea boot with an arch-support footbed for all-day comfort. Pull-on style with elastic gore insets Leather upper and lining/rubber sole Made... more

$475.00

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Burkett Cap Toe Boot

Burkett Cap Toe Boot

Men's To Boot New York Burkett Cap Toe Boot - Black - Casual boots Polished calfskin leather adds sophisticated shine to a classic Italian boot with a smart arch-support insole and flexible rubber sole. Lace-up style Removable, cushioned insole with... more

$495.00 $297.00

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Richard Chukka Boot

Richard Chukka Boot

Men's To Boot New York Richard Chukka Boot - Brown - Casual boots Soft suede adds a laid-back vintage-inspired touch to this dapper Italian-made chukka boot built on a sturdy leather sole featuring grippy rubber tread. Leather upper and lining/rubber... more

$450.00

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Belvedere Zip Boot

Belvedere Zip Boot

Men's To Boot New York Belvedere Zip Boot - Brown - Casual boots Burnished calfskin leather elevates a stylish Italian boot fitted with a smart side zipper and comfortable arch support. Side zip closure Arch support Leather upper, lining and sole Made... more

$595.00

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Belvedere Zip Boot

Belvedere Zip Boot

Men's To Boot New York Belvedere Zip Boot - Brown - Casual boots Burnished calfskin leather elevates a stylish Italian boot fitted with a smart side zipper and comfortable arch support. Side zip closure Arch support Leather upper, lining and sole Made... more

$595.00

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Perry Venetian Loafer

Perry Venetian Loafer

Men's To Boot New York Perry Venetian Loafer - Black - Loafers A fine grosgrain overlay tops a stylish Italian loafer fashioned from calfskin patent leather. Leather and textile upper/leather lining and sole Made in Italy Men's Shoes. more

$399.00

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Palo Alto Driving Shoe

Palo Alto Driving Shoe

Men's To Boot New York Palo Alto Driving Shoe - Brown - Loafers Premium leather construction elevates a casually charming driving shoe featuring cushioned arch support. Leather upper and lining/rubber sole Made in Italy Men's Shoes. more

$350.00

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Mitchum Driving Shoe

Mitchum Driving Shoe

Men's To Boot New York Mitchum Driving Shoe - Brown - Loafers Smart suede construction elevates a clean-cut Italian driving shoe topped with a crisp penny strap. Suede upper/leather lining/rubber sole Made in Italy Men's Shoes. more

$325.00 $195.00

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Del Amo Driving Shoe

Del Amo Driving Shoe

Men's To Boot New York Del Amo Driving Shoe - Brown - Loafers A sleek gunmetal bit tops off a classic Italian driving shoe fashioned from supple suede or leather. Leather upper and lining/rubber sole Made in Italy Men's Shoes. more

$350.00 $245.00

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Driving Shoe

Driving Shoe

Men's To Boot New York Driving Shoe - Gray - Loafers Bold contrast stitching defines a charming Italian driving shoe fitted with cushioned arch support for comfort that lasts. Slip-on style Suede upper/leather lining/rubber sole Made in Italy Men's Shoes. more

$325.00

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Driving Shoe

Driving Shoe

Men's To Boot New York Driving Shoe - Blue - Loafers Bold contrast stitching defines a charming Italian driving shoe fitted with cushioned arch support for comfort that lasts. Slip-on style Suede upper/leather lining/rubber sole Made in Italy Men's Shoes. more

$325.00

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Keiran Loafer

Keiran Loafer

Men's To Boot New York Keiran Loafer - Brown - Loafers Plush suede construction elevates a fine Italian loafer designed for the workplace and beyond. Leather upper, lining and sole Made in Italy. more

$450.00

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Bower Monk Strap Shoe

Bower Monk Strap Shoe

Men's To Boot New York Bower Monk Strap Shoe - Brown - Monk shoes Supple Italian suede lends undeniable style to a handsome monk-strap shoe cushioned by a plush insole with arch support. more

$450.00

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Amedeo Derby

Amedeo Derby

Men's To Boot New York Amedeo Derby - Brown - Derbies Burnished leather and a plain toe lend modern sophistication to an Italian leather derby outfitted with a cushioned footbed for lasting comfort. Cushioned footbed with arch support Leather upper and... more

$399.00

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Magnus Driving Shoe

Magnus Driving Shoe

Men's To Boot New York Magnus Driving Shoe - Black - Loafers Woven calfskin leather adds rich texture to a classic Italian driving shoe with smart arch support. Leather upper and lining/rubber sole Made in Italy. more

$350.00

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Stone Slip-on Sneaker

Stone Slip-on Sneaker

Men's To Boot New York Stone Slip-on Sneaker - Black - Low-top sneakers Creamy suede construction defines a versatile Italian slip-on with an arch-support footbed. Leather upper and lining/rubber sole Made in Italy. more

$425.00

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Bolla Sneaker

Bolla Sneaker

Men's To Boot New York Bolla Sneaker - White - Low-top sneakers Clean, contemporary style meets optimal comfort in this pebbled-leather sneaker set on a lightweight rubber sole. Pull-on style with elastic laces Removable, cushioned insole with arch... more

$450.00

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Amedeo Derby

Amedeo Derby

Men's To Boot New York Amedeo Derby - Brown - Derbies Polished leather and a plain toe lend modern sophistication to an Italian derby outfitted with a cushioned footbed for lasting comfort. Cushioned footbed with arch support Leather upper and... more

$399.00

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Cassidy Moc Toe Loafer

Cassidy Moc Toe Loafer

Men's To Boot New York Cassidy Moc Toe Loafer - Blue - Loafers Step into breathable comfort with this flexible moc-toe loafer with a supple leather lining and arch support. Removable insole with arch support Leather upper and lining/rubber sole Made in... more

$365.00

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Tesoro Penny Loafer

Tesoro Penny Loafer

Men's To Boot New York Tesoro Penny Loafer - Gray - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

$399.00

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Amedeo Derby

Amedeo Derby

Men's To Boot New York Amedeo Derby - Brown - Derbies Burnished leather and a plain toe lend modern sophistication to an Italian leather derby outfitted with a cushioned footbed for lasting comfort. Cushioned footbed with arch support Leather upper and... more

$399.00 $279.30

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Stone Slip-on Sneaker

Stone Slip-on Sneaker

Men's To Boot New York Stone Slip-on Sneaker - Brown - Low-top sneakers Creamy suede construction defines a versatile Italian slip-on with an arch-support footbed. Leather upper and lining/rubber sole Made in Italy. more

$425.00

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Magnus Driving Shoe

Magnus Driving Shoe

Men's To Boot New York Magnus Driving Shoe - Brown - Loafers Woven calfskin leather adds rich texture to a classic Italian driving shoe with smart arch support. Leather upper and lining/rubber sole Made in Italy. more

$350.00

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Thorpe Leather Loafer

Thorpe Leather Loafer

Men's To Boot New York Thorpe Leather Loafer - Brown - Loafers A sleek, minimalist silhouette lends sophisticated style to an Italian loafer fashioned from soft calfskin leather. Removable insole Leather upper, lining and sole Made in Italy. more

$399.00

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Dickerson Penny Loafer

Dickerson Penny Loafer

Men's To Boot New York Dickerson Penny Loafer - Black - Loafers A classic penny keeper and sleek leather construction lend timeless sophistication to a polished loafer perfect for any occasion. Leather upper and lining/leather and rubber sole Made in... more

$425.00

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Amedeo Derby

Amedeo Derby

Men's To Boot New York Amedeo Derby - Black - Derbies Burnished leather and a plain toe lend modern sophistication to an Italian leather derby outfitted with a cushioned footbed for lasting comfort. Cushioned footbed with arch support Leather upper and... more

$399.00

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Nico Oxford

Nico Oxford

Men's To Boot New York Nico Oxford - Brown - Oxfords A sueded inside heel and flexible outsole elevate the comfort of a polished leather oxford cushioned by an arch-supporting insole. Lace-up style Cushioned insole with arch support Removable insole... more

$450.00

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Ainsworth Sneaker

Ainsworth Sneaker

Men's To Boot New York Ainsworth Sneaker - Brown - Low-top sneakers Debossed logo lettering on the tongue elevates this napa leather sneaker cushioned by plush arch support. Removable, cushioned insole with arch support Leather upper and lining/rubber... more

$425.00

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Jett Derby

Jett Derby

Men's To Boot New York Jett Derby - Brown - Derbies A supple suede upper and streamlined silhouette distinguish a sophisticated derby grounded by a durable rubber cupsole for modern appeal. Lace-up style Cushioned footbed with arch support Leather... more

$360.00

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Agostino Bit Loafer

Agostino Bit Loafer

Men's To Boot New York Agostino Bit Loafer - Black - Loafers A polished bit adds dapper appeal to an Italian leather loafer designed with a timeless apron toe for a style that will take you from desk to dinner with ease. Cushioned insole with arch... more

$399.00 $250.01

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